Molecular engineering of 1, 3, 5-triaryl-2-pyrazoline fluorescent logic systems responsive to acidity and oxidisability and attachment to polymer beads. Issue 1 (8th December 2020)

• Record Type: Journal Article
• Authors: Zerafa, Nicole; Cini, Miriam; Magri, David C.
• Is Part Of: Molecular Systems Design and Engineering. Volume 6:Issue 1(2021)
• Page Start: 93
• Page End: 99
• Publication Date: 2020-12-08
• Subjects: Chemistry -- Molecular aspects -- Periodicals; Chemical engineering -- Molecular aspects -- Periodicals; Nanotechnology -- Periodicals; 620.5
• DOI: 10.1039/d0me00136h
• Languages: English
• ISSNs: 2058-9689

Abstract

Abstract : Designed fluorescent logic gates based on PET and ICT emulating NOT, off–on–off and INHIBIT logic functions are covalently attached to PEG–polystyrene polymer beads. Abstract : 1, 3, 5-Triaryl-2-pyrazolines were designed, synthesised and covalently immobilised onto submillimetre TentaGel® polystyrene beads (functionalised with amino-terminated polyethyleneglycol ligands) by peptide bond formation. The molecules are modularly designed based on photoinduced electron transfer (PET) according to electron-donor–spacer–fluorophore–receptor and receptor 1 –spacer–fluorophore–receptor formats with ferrocene and N, N -dimethylaniline as the electron donor and receptor1 . A reference fluorophore–receptor compound, associated with an internal charge transfer (ICT) mechanism, is included for comparison. A carboxylate moiety at the para -position of the 1-phenyl ring assists the molecules with aqueous solubility and serves as the site for covalent attachment to the polystyrene beads. The H +, Fe 3+ -driven INHIBIT, H + -driven off–on–off and H + -driven NOT logic systems are demonstrated in aqueous methanol and attached onto heterogeneous polymer submillimeter beads. The INHIBIT gate was tested with the stronger oxidant, ammonium persulfate, which resulted in a greater fluorescence quantum yield ( Φ f = 0.192). A double-tagged polymer bead integrating INHIBIT and off–on–off multi-valued logic was also prepared.